This invention relates to condensed ring aromatic ureas and isoureas which are useful as agricultural chemicals.
Netherlands Pat. No. 121,788, published on Sept. 15, 1966, discloses the preparation of compounds of Formula 1 and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 Z is methyl or methoxy. PA1 Z is methyl or methoxy. PA1 A and A.sup.2 are independently ##STR9## Cl, F, Br, NO.sub.2, --CH.sub.3, --SO.sub.2 NR.sup.1 R.sup.2, --SO.sub.2 N(CH.sub.3)(OCH.sub.3), --S(O).sub.n R.sup.3, --OR.sup.3, --OSO.sub.2 R.sup.3 or --OSO.sub.2 CF.sub.3 ; PA1 B is ##STR10## n is 0, 1 or 2; Q is O, S or NR.sup.7 ; PA1 R.sup.1 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.2 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.3 is C.sub.1 -C.sub.4 alkyl; PA1 R.sup.4 is H or CH.sub.3 ; PA1 R.sup.5 is ##STR11## R.sup.6 is C.sub.1 -C.sub.6 alkyl; R.sup.7 is H, --OCH.sub.3 or C.sub.1 -C.sub.4 alkyl; when Q is O or S then R.sup.8 is C.sub.1 -C.sub.6 alkyl; C.sub.3 -C.sub.6 alkenyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, phenyl, benzyl, or phenyl or benzyl substituted with one or two groups selected from CH.sub.3, Cl or OCH.sub.3 ; and when Q is O, R.sup.8 may also be CH.sub.2 CH.sub.2 Cl; when Q is R.sup.7 then R.sup.8 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl and R.sup.8 and R.sup.7 taken together can be --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- and with the proviso that when R.sup.7 is CH.sub.3 O, R.sup.8 is CH.sub.3 ; PA1 R.sup.9 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, benzyl, benzyl substituted with one or two groups selected from CH.sub.3, Cl or OCH.sub.3 ; PA1 R.sup.10 is H or CH.sub.3 ; PA1 R.sup.11 is C.sub.1 -C.sub.3 alkyl; PA1 R.sup.12 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 alkenyl; PA1 T is O or N-OR.sup.12 ; PA1 W is O or S; PA1 X is CH.sub.3, CH.sub.3 O or CH.sub.3 CH.sub.2 O; PA1 X.sup.2 is O or CH.sub.2 ; PA1 Y is H, C.sub.1 -C.sub.3 alkyl, CH.sub.3 OCH.sub.2, CH.sub.3 CH.sub.2 OCH.sub.2, OCH.sub.2 CO.sub.2 --(H or C.sub.1 -C.sub.2 alkyl), OCH(CH.sub.3)CO.sub.2 (H or C.sub.1 -C.sub.2 alkyl), O--(C.sub.1 -C.sub.3 alkyl), O--(C.sub.3 -C.sub.4 alkenyl) or NR.sup.10 R.sup.11 ; PA1 Y.sup.1 is H, CH.sub.3 or OCH.sub.3 ; PA1 Y.sup.2 is H or CH.sub.3 ; and PA1 Z is N, CH or CCH.sub.3 ; PA1 (1) Compounds of formula 5 in which ##STR12## (2) Compounds of formula 6 in which ##STR13## PA1 (3) Compounds of preferred 1 in which A is Cl, NO.sub.2, CH.sub.3, CH.sub.3 O, CH.sub.3 SO.sub.2 O, CH.sub.3 SO.sub.2, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 N(CH.sub.3)(OCH.sub.3), CH.sub.3 S or CH.sub.3 SO; PA1 (4) Compounds of preferred 3 in which A.sup.1 is H; PA1 (5) Compounds of preferred 4 in which Y is CH.sub.3 or CH.sub.3 O; X.sup.2 is O, and Y.sup.2 is CH.sub.3 ; PA1 (6) Compounds of preferred 5 in which A is Cl; PA1 (7) Compounds of preferred 2 in which A.sup.2 is Cl, NO.sub.2, CH.sub.3, CH.sub.3 O, CH.sub.3 SO.sub.2 O, CH.sub.3 SO.sub.2, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 N(CH.sub.3)(OCH.sub.3), CH.sub.3 S or CH.sub.3 SO; PA1 (8) Compounds of preferred 7 in which A.sup.1 is H; PA1 (9) Compounds of preferred 8 in which X.sup.2 is O, Y is CH.sub.3 or CH.sub.3 O and Y.sup.2 is CH.sub.3 ; PA1 (10) Compounds of preferred 9 in which A.sup.2 is Cl.
U.S. Pat. No. 4,127,405, issued to Levitt on Nov. 28, 1978, discloses compounds of Formula 2, their agriculturally suitable salts, and methods of using them as selective, as well as general, herbicides having both pre-emergence and post-emergence activity: ##STR2## wherein R.sub.1 can be selected from several aromatic possibilities including ##STR3## W is oxygen or sulfur; X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 ; and
U.S. Pat. No. 4,120,691, issued to Levitt on Oct. 17, 1978, discloses compounds of Formula 3, their agriculturally suitable salts, and methods of using them as general herbicides having both pre-emergence and post-emergence activity and as plant growth regulants: ##STR4## wherein R.sub.1 can be selected from several aromatic possibilities including ##STR5## W is oxygen or sulfur; and X and Z are independently hydrogen, methyl or methoxy.
U.S. Pat. No. 4,169,719, issued to Levitt on Oct. 2, 1979, discloses compounds of Formula 4, their agriculturally suitable salts, and methods of using them as selective, as well as general, herbicides having both pre-emergence and post-emergence activity: ##STR6## wherein R.sub.1 can be selected from several aromatic possibilities including ##STR7## W is oxygen or sulfur; X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products which satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. Also, for man to conduct manufacturing, transportation, communications and other such activities, he must wage a constant battle to prevent encroachment of undesirable vegetation into areas where such activities are performed.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. A need still exists, however, for more effective herbicides.